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When Jack Armstrong was a kid, Farrell's was the sort of expat Irish bar cops would stop by for an early-evening traveller.

The neighbourhood around it in Prospect Park has come up. Farrell's remains resolutely down-market – a fireman's bar, a bus driver's bar.

"You won't see no one reading no New York Times in here," Armstrong says.

Technically, it's Farrell's Bar & Grill. There is no grill. Or food of any sort. They sell beer in quart Styrofoam cups. Six bucks each. By metric conversion, a quart works out to Far Too Much Beer.

Mid-afternoon, it's rammed and raucous. They gave in a couple of years ago and put in a stereo. If there is a theme to the crowd, it's "tattoos you should have thought a little harder about."

Armstrong, 51, grew up a few minutes from here, in Flatbush. He hasn't been to Farrell's in a decade. We're in there an hour and word gets out. Lumpy, vaguely dangerous-looking guys he played grade-school ball with at St. Brendan's parish start rolling in to pay respects.

"So I hear you're a big deal in Canada," one of them says suspiciously.

Armstrong demurs. But it's true. He is a big deal in Canada.

When you think of Toronto Raptors basketball, the narration that runs through your mind is probably Armstrong's nasal Brooklyn twang. He's been working as the team's on-air analyst, starting with radio before moving to TV, for 16 years. Analysts are not supposed to be the stars. The play-by-play guy generally dominates conversation. But Armstrong's voice is so signature and simpatico – he sounds like a kid gargling rock salt – it's taken over. On camera, he's an impish Irish uncle, the guy having too much fun "working."

When he's excited about something, which is often, his consonants disappear. True Brooklyn is almost all vowels: 'Gedoudaheeaah!"

Mid-game, Armstrong's talent is walking the line between homerism and piling on. His critiques are both pointed and gentle. Armstrong calls this style "first guessing."

"I try to imagine what I would do, and tell people that. I don't second guess," Armstrong says, shrugging. "But I was 100-154 in my coaching career, so whadda I know?"

Beyond the voice and the analysis, that's the secret. Armstrong takes the game seriously, but not himself. His entire mien is shot through with a wondrous, how-did-I-ever-get-so-lucky slant that may be explained by his upbringing.

His parents, both Irish immigrants, met at a dance in the Bronx. His father died when Jack was 7. Mary Armstrong raised four boys alone while working the lunch counter at PS 238.

They lived in a four-room apartment. Jack and his brother Brendan slept together on a pullout couch in the living room. The brothers shared a paper route between themselves for 20 years. That's how they paid for a private high school.

Jack grew up playing ball, and not particularly well. But he had a Jesuitical cast of mind, an obsessive work ethic and an incurable case of Can Do'ism. From the '70s to the mid-'80s, New York City was the centre of the basketball universe. Armstrong threw himself into its midst, taking any opportunity to volunteer at a camp, coach at his alma maters and, most importantly, make a friend in the game.

He was a graduate assistant at Fordham while getting his masters. He beat out Jeff Van Gundy for the head assistant job at Niagara University. When the coach was fired after a year, Armstrong was given the top job and a (very) small raise.

"They brought me in and told me they'd pay me $25,000. At the time, most head coaches were getting 90, 100. They asked me to keep the number to myself. And I said, 'Don't worry. I'm embarrassed by it, too.' "

Armstrong was 26 years old – the youngest head coach in NCAA Division I.

Ten years on, he was married and a father. (Jack and his wife, Dena, eventually adopted three sons.) He was also burnt out. Niagara did him the favour of firing him. By the terms of his contract, he was still being paid for another year, and thought he might try broadcasting. He made a demo. Someone suggested he send it up to the FAN 590, the Raptors' radio carrier. They passed. Armstrong rallied his pals in the coaching mafia – no one has more pals. They besieged the station with phone calls and references.

"Eventually, they call me back and say, 'We surrender.' That's how I got the job."

Sixteen years later, he's a regular on TSN, NBA-TV and ESPN, a surrogate, on-air coach for an entire country. Life is strange and, when you are good to it, it's often good back.

Jack turns to Ed the bartender for another Styrofoam bucket of "Irish Courage." Ed's formulation, not mine. My notes have become incomprehensible.

Does he feel conflicted about the Nets? Jack grew up rooting for them when they were an ABA team in New Jersey.

"Not at all [long comedic pause; a smile hauls up both sides of his face]. They don't sign my cheques."

The group howls in delight. (The rest of them are Knicks fans.)

We're now into neighbourhood gossip. This one is sick. That one is "a little jammed up" (i.e. in jail). They're closing Holy Name, where grade-school Jack used to get torched by future Hall of Famer Chris Mullin. They glance by local guys that didn't make it through 9/11 – Farrell's regulars, first-responders, brokers. Jack figures he lost almost a dozen friends, and he doesn't like talking about it.

They are so deep into Brooklyn argot, the conversation is difficult to follow.

Someone wonders if Jack will ever come home. They moved his mom out to a place near Rockaway Park a few years back. He lives in Lewiston, just the other side of the Canada-U.S. border.

All the other Armstrong boys have scattered, chasing work as engineers and executives. They've done alright – four kids raised in a four-room apartment.

"I don't know," Jack says. "I don't know what I'm gonna do when I grow up. But right now, I'm happy …"

He raises his cup.

"… and you don't (expletive) with happy."

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